What happens when the person behind the podcast steps in front of the camera?

With Drew out this week, Get Over It producer Venus joins Heidi for a conversation that goes pretty much everywhere… but somehow keeps coming back to the same question: What happens when life forces you to get uncomfortable?

It starts with Venus admitting that after years of inviting successful people to speak on panels, she found herself asking the exact question that drives her crazy when she hears it from other women: Are you sure I should be up there?

From there, Venus and Heidi get into self-doubt, feeling like you have to be overprepared before you deserve a seat at the table, and the expectations we put on ourselves as women, professionals, and leaders.

They also get personal about getting older, taking care of yourself differently as your body changes, setting boundaries, navigating grief, and learning that protecting yourself isn’t always the same thing as avoiding something.

Heidi opens up about rebuilding her life and career after the end of an 18-year relationship, including intentionally doing things that made her uncomfortable as she figured out who she wanted to become next. Now, finding herself in another rut, she realizes it might be time to do it all over again.

In This Episode, Heidi & Venus Discuss:

• Why successful women still question whether they deserve a seat at the table
• The pressure to be overprepared before putting yourself out there
• Fear of criticism and looking like you don’t know what you’re doing
• Getting older and realizing you definitely do not have everything figured out
• Paying more attention to your health as your body changes
• Setting boundaries when you’re used to taking care of everyone else
• The difference between avoiding something and protecting yourself
• Navigating grief and finding ways to keep moving forward
• Turning difficult experiences into empathy for someone else
• Looking for the lesson when things don’t go your way
• Starting over personally and professionally
• Why Heidi intentionally made herself uncomfortable when rebuilding her career
• Recognizing when you’re in a rut and need to shake things up

Growth doesn’t always look like having the answers.

Sometimes it looks like admitting you’re uncomfortable, doing the thing anyway, and figuring out who you are on the other side.

🎙️ Listen to the new episode of Get Over It wherever you get your podcasts.

When was the last time you stopped and asked yourself what you’re actually proud of?

Not what you accomplished. Not what you checked off the list. Not what you could have done better.

What are you genuinely proud of?

In this episode of Get Over It, Heidi shares what happened when a rough weekend sent her into full self-examination mode and led her to create a simple exercise built around three questions: What are you proud of? What are you excited about? And what brings you joy?

Of course, she made Drew do it too.

What starts as a simple exercise turns into a much bigger conversation about success, ambition, comparison, and the pressure to always be doing more. Drew and Heidi unpack why it can be so difficult to acknowledge our own wins without immediately adding a “but,” especially when life or business doesn’t look the way we thought it would.

They also explore what happens when the things that once motivated you no longer do. When accomplishments, money, accolades, and being the best start to matter less, how do you redefine success? And what if the things bringing you the most joy are actually the quiet, ordinary parts of your life?

In This Episode, Drew & Heidi Discuss:

• Why saying “I’m proud of myself” can feel so uncomfortable
• The difference between an accomplishment and something you’re genuinely proud of
• Why we immediately minimize our own wins
• Comparing where you are today to a past version of yourself
• The pressure to constantly do more and achieve more
• What happens when your definition of success starts to change
• Why accomplishments and joy don’t always come from the same places
• Finding motivation when competition and achievement no longer drive you
• Using your past as evidence of what you’re capable of
• Learning to recognize when you’ve done enough
• The simple three-part exercise Drew and Heidi use to reflect on where they’ve been and where they’re going

Maybe the goal isn’t to keep moving the finish line every time you reach it.

Maybe sometimes you need to stop long enough to realize there’s already a lot to be proud of.

🎙️ Listen to Get Over It wherever you get your podcasts, and try the exercise along with Drew and Heidi: What are you proud of? What are you excited about? And what brings you joy?

What happens when someone you’ve worked with for years decides it’s time to leave?

When a longtime member of Drew’s team decides to go out on his own, it brings up a bigger question: Should your team really feel like family?

In this episode of Get Over It, Drew and Heidi talk about the complicated relationship between leadership, loyalty, and letting people grow. They get into why an employee leaving can feel so personal, how leaders can become overly responsible for the people they work with, and why someone choosing a new path doesn’t necessarily mean something went wrong.

Heidi shares her own experiences with longtime team members moving on and what she’s learned from working alongside her daughter, while Drew wrestles with the realization that sometimes a great leader’s job isn’t to keep people, it’s to help them grow, even if that growth eventually takes them somewhere else.

They also dig into workplace boundaries, different communication styles, showing appreciation in ways people actually value, the danger of creating “golden handcuffs,” and why putting relationships first doesn’t mean avoiding the hard conversations.

In This Episode, Drew & Heidi Discuss:

• Should your team really feel like family?
• Why an employee leaving can feel like a personal betrayal
• How leaders can separate someone else’s decision from their own self-worth
• Leading people without taking responsibility for every part of their success
• Working with actual family in a family business
• Understanding how different team members communicate and process conflict
• Why great employees sometimes outgrow their roles
• The difference between helping people stay and making them feel trapped
• Creating healthy boundaries between relationships and business
• Why strong workplace relationships still require honesty and accountability
• Learning to let people grow, even when that means letting them go

Because maybe the goal of great leadership isn’t to build a team that never leaves.

Maybe it’s to build people who are capable of choosing what comes next.

🎙️ Listen to Get Over It wherever you get your podcasts, and send this episode to a leader, business owner, or teammate who needs to hear this conversation.